Rhodium(I)-Catalyzed Cycloisomerization of 1,6-Enynes

被引:1
|
作者
Matsushima, Yuji [1 ]
Phillips, Eric M. [1 ]
Bergman, Robert G. [2 ]
Ellman, Jonathan A. [1 ]
机构
[1] Yale Univ, Dept Chem, New Haven, CT 06520 USA
[2] Univ Calif Berkeley, Lawrence Berkeley Natl Lab, Dept Chem, Berkeley, CA 94720 USA
关键词
rhodium; homogeneous catalysis; ring closure; isomerization; enones; C-H ACTIVATION; ALPHA; BETA-UNSATURATED KETOXIMES; ENYNE METATHESIS; ALKYNES; PYRIDINES; BOND; TETRAHYDROPYRIDINES; FUNCTIONALIZATION; CYCLIZATION; CATALYSIS;
D O I
10.1055/s-0034-1380359
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
A new and unexpected rhodium(I)-catalyzed cycloisomerization of 1,6-enynes is reported. Several different alkyne substitution patterns were evaluated under the reaction conditions, including a deuterated derivative that provides some insight into the reaction mechanism.
引用
收藏
页码:1533 / 1536
页数:4
相关论文
共 50 条
  • [1] Rhodium(I)-Catalyzed Cycloisomerization of 1,6-Enynes to Bicyclo[4.1.0]heptenes
    Kim, Sun Young
    Chung, Young Keun
    JOURNAL OF ORGANIC CHEMISTRY, 2010, 75 (04): : 1281 - 1284
  • [2] Enantioselective Rhodium-Catalyzed Cycloisomerization of (E)-1,6-Enynes
    Deng, Xu
    Ni, Shao-Fei
    Han, Zheng-Yu
    Guan, Yu-Qing
    Lv, Hui
    Dang, Li
    Zhang, Xu-Mu
    ANGEWANDTE CHEMIE-INTERNATIONAL EDITION, 2016, 55 (21) : 6295 - 6299
  • [3] Cycloisomerization of 1,6-enynes catalyzed by transition metals
    Tong, XF
    Zhang, ZG
    CHINESE JOURNAL OF ORGANIC CHEMISTRY, 2004, 24 (06) : 591 - 599
  • [4] Novel rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift
    Tong, XF
    Zhang, ZG
    Zhang, XM
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2003, 125 (21) : 6370 - 6371
  • [5] Novel rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift
    Zhang, Z. (xumu@chem.psu.edu), 1600, American Chemical Society (125):
  • [6] The gold(I)-catalyzed cycloisomerization of 1,6-enynes to 1,4-dienes
    Lee, Sang Ick
    Kim, Soo Min
    Kim, Sun Young
    Chung, Young Keun
    SYNLETT, 2006, (14) : 2256 - 2260
  • [7] Enantioselective Cycloisomerization of 1,6-Enynes to Bicyclo[3.1.0]hexanes Catalyzed by Rhodium and Benzoic Acid
    Masutomi, Koji
    Noguchi, Keiichi
    Tanaka, Ken
    JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, 2014, 136 (21) : 7627 - 7630
  • [8] Enantioselective cycloisomerization of 1,6-enynes to bicyclo[3.1.0]hexanes catalyzed by rhodium and benzoic acid
    Tanaka, K. (ktanaka@apc.titech.ac.jp), 1600, American Chemical Society (136):
  • [9] Rhodium-catalyzed cycloisomerization of 1,6-enynes with an intramolecular halogen shift: Reaction scope and mechanism
    Zhang, Z. (zhaoguo@mail.sioc.ac.cn), 1600, American Chemical Society (126):
  • [10] Cationic Rhodium(I)-Catalyzed Asymmetric Cyclohydroformylation of 1,6-Enynes with Formaldehyde
    Hayashi, Erin
    Akiyama, Naoto
    Kakiuchi, Kiyomi
    Kawai, Tsuyoshi
    Morimoto, Tsumoru
    CHEMISTRY-AN ASIAN JOURNAL, 2023, 18 (05)